NZ526580A - Quinuclidine carbamate derivatives and their use as M3 antagonists - Google Patents
Quinuclidine carbamate derivatives and their use as M3 antagonistsInfo
- Publication number
- NZ526580A NZ526580A NZ526580A NZ52658001A NZ526580A NZ 526580 A NZ526580 A NZ 526580A NZ 526580 A NZ526580 A NZ 526580A NZ 52658001 A NZ52658001 A NZ 52658001A NZ 526580 A NZ526580 A NZ 526580A
- Authority
- NZ
- New Zealand
- Prior art keywords
- octane
- azoniabicyclo
- group
- bromide
- trifluoroacetate
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title claims description 7
- DSTLXMSUVMLNBP-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;carbamate Chemical class NC(O)=O.C1CC2CCN1CC2 DSTLXMSUVMLNBP-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 247
- -1 furan-2-ylmethyl Chemical group 0.000 claims abstract description 117
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 238000006467 substitution reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 191
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 132
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 41
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 24
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- 239000000203 mixture Substances 0.000 claims description 23
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
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- WKFZHVFBHYHYAK-UHFFFAOYSA-N benzyl(phenyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CC1=CC=CC=C1 WKFZHVFBHYHYAK-UHFFFAOYSA-N 0.000 claims description 7
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- JEEPGBSHIOBHQN-GDWJQBMWSA-N [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 JEEPGBSHIOBHQN-GDWJQBMWSA-N 0.000 claims description 2
- FWPIWVUMKDFZSR-JOMKWTIYSA-N [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-3-ylmethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC3=CSC=C3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 FWPIWVUMKDFZSR-JOMKWTIYSA-N 0.000 claims description 2
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- OLTPKMBOLARPFC-UHFFFAOYSA-N phenyl(2-phenylethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CCC1=CC=CC=C1 OLTPKMBOLARPFC-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
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- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200003084 | 2000-12-22 | ||
| PCT/EP2001/015169 WO2002051841A1 (en) | 2000-12-22 | 2001-12-20 | Quinuclidine carbamate derivatives and their use as m3 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ526580A true NZ526580A (en) | 2005-04-29 |
Family
ID=8496114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ526580A NZ526580A (en) | 2000-12-22 | 2001-12-20 | Quinuclidine carbamate derivatives and their use as M3 antagonists |
Country Status (32)
Families Citing this family (120)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| TR200400420T4 (tr) * | 2000-06-27 | 2004-03-22 | Laboratorios S.A.L.V.A.T., S.A. | Arilalkilaminlerden türetilmiş karbamatlar. |
| JP4445704B2 (ja) | 2000-12-22 | 2010-04-07 | アルミラル・ソシエダッド・アノニマ | キヌクリジンカルバメート誘導体およびｍ３アンダゴニストとしてのそれらの使用 |
| UA75626C2 (en) | 2000-12-28 | 2006-05-15 | Almirall Prodesfarma Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| CA2470567A1 (en) | 2001-12-14 | 2003-06-26 | Targacept, Inc. | Methods and compositions for treatment of central nervous system disorders |
| UA76571C2 (en) | 2001-12-20 | 2006-08-15 | Derivatives of 1-alkyl-1-azoniabicyclo [2.2.2.]octanecarbamate and use thereof as antagonists of muscarin receptor | |
| ES2203327B1 (es) | 2002-06-21 | 2005-06-16 | Almirall Prodesfarma, S.A. | Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen. |
| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| EA200500173A1 (ru) * | 2002-07-08 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные 3,6-дизамещенного азабицикло[3.1.0]гексана в качестве антагонистов мускариновых рецепторов |
| TWI295669B (en) | 2002-10-30 | 2008-04-11 | Theravance Inc | Substituted 4-amino-1-(pyridylmethyl) piperidine and related compounds |
| PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| AU2003214520A1 (en) | 2003-04-09 | 2004-11-01 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| AU2004228452A1 (en) | 2003-04-11 | 2004-10-21 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| ES2329133T3 (es) | 2003-05-28 | 2009-11-23 | Theravance, Inc. | Compuestos azabicicloalcanicos como antagonistas de receptores de muscarinicos. |
| WO2005007645A1 (en) | 2003-07-11 | 2005-01-27 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
| US7345060B2 (en) | 2003-11-21 | 2008-03-18 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| US7456199B2 (en) | 2004-03-11 | 2008-11-25 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| WO2005087739A1 (en) | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TWI341836B (en) | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7265133B2 (en) | 2004-03-11 | 2007-09-04 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7501442B2 (en) | 2004-03-11 | 2009-03-10 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| WO2005087737A1 (en) | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| WO2005087736A1 (en) | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TW200538095A (en) | 2004-03-11 | 2005-12-01 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| ES2246170B1 (es) * | 2004-07-29 | 2007-04-01 | Almirall Prodesfarma, S.A. | Nuevo procedimiento para preparar derivados de carbamato de quinuclidinio. |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| EP1866284A1 (en) | 2005-03-10 | 2007-12-19 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2008533028A (ja) | 2005-03-10 | 2008-08-21 | セラヴァンス， インコーポレーテッド | ムスカリン性受容体アンタゴニストとして有用なビフェニル化合物 |
| TW200714587A (en) | 2005-03-10 | 2007-04-16 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
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| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
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| TW200825084A (en) * | 2006-11-14 | 2008-06-16 | Astrazeneca Ab | New compounds 521 |
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| RU2441868C2 (ru) * | 2007-02-09 | 2012-02-10 | Астеллас Фарма Инк. | Аза-кольцевое соединение с внутренним мостиком |
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